14870-72-5

Basic information

• Product Name: 1,4-dimethyl-1,4-diazoniabicyclo[2.2.2]octane
• CAS NO: 14870-72-5
• Molecular Formula: C₈H₁₈N₂*2I
• Molecular Weight: 142.2408
• Mol File: 14870-72-5.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: 1,4-dimethyl-1,4-diazoniabicyclo[2.2.2]octane(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-dimethyl-1,4-diazoniabicyclo[2.2.2]octane(14870-72-5)
• EPA Substance Registry System: 1,4-dimethyl-1,4-diazoniabicyclo[2.2.2]octane(14870-72-5)

Safety Data

• Hazardous Substances Data: 14870-72-5(Hazardous Substances Data)

Usage

Molecular structure

Bicyclic with two nitrogen atoms and two methyl groups

Type of compound

Heterocyclic compound

Physical state

Colorless to pale yellow liquid

Odor

Characteristic amine-like

Role in organic synthesis

Catalyst and reagent

Properties

Strong non-nucleophilic base

Applications in reactions

a. Knoevenagel condensations
b. Michael additions
c. Baylis-Hillman reactions

Industrial applications

Curing agent in the production of polyurethane foams and resins

Versatility

Useful in various chemical reactions and industrial applications

Upstream product

• 280-57-9 1,4-diaza-bicyclo[2.2.2]octane 
• 74-88-4 methyl iodide 

Relevant articles and documents

Dihydrogen phosphate and hydrogen sulphate of 1,4-dimethyl-1,4- diazabicyclo[2.2.2]octane-1,4-diium: Crystal structures, hydrogen bonding and infrared spectra

The crystal structures of the title compounds consist of 1,4-dimethyl-1,4-diazabicyclo[2.2.2]octane-1,4-diium cation [C8H 18N2]2+ and [H2PO4] - or [HSO4]- anions. Both crystal structures are monoclinic, the structure of the dihydrogen phosphate (I) is non-centrosymmetric (P21) with a = 6.4090(2) A, b = 13.6920(5) A, c = 7.6140(3) A, β = 94.620(2)°, V = 665.97(4) A3, Z = 2; whereas the unit cell of the hydrogen sulphate (II) is centrosymmetric (P21/c) with a = 13.8460(2) A, b = 12.6610(2) A, c = 8.0360(2) A, β = 99.5800(12)°, V = 1389.10(5) A3, Z = 4. Both the structures are formed by the different bonding patterns of the anions interlinked by strong and moderate O-H???O hydrogen bonds. While the structure of (I) consists of a two-dimensional network of the hydrogen bonded dihydrogen phosphates, the infinite chains of the hydrogen bonded hydrogen sulphates are the basic building unit of the structure (II). In addition to the dominant electrostatic interaction the divalent cations stabilize themselves in the structures by forming several C-H???O hydrogen bonds to the oxygen atoms of the anions. The IR spectra of both the compounds are strongly affected by the hydrogen bonds whose influence on OH stretching vibrations is analysed by means of the DFT calculations in the solid state.

A convenient synthesis of [11C]paraquat and other [N-methyl-11C]bisquaternary ammonium compounds

[11C]Paraquat was synthesized by the reaction of [11C]methyl triflate with the mono-triflate salt of 1-methyl-[4,4′]bipyridinyl. The product was selectively separated from the precursor by a microcolumn of Chelex 100 ion exchange resin. The method was applied to the synthesis of a variety of [N-methyl-11C]bisquaternary ammonium compounds. This is the first reported use of a chelating cation exchange resin for the selective purification of organic dications. Copyright

Controlling the Recognition and Reactivity of Alkyl Ammonium Guests Using an Anion Coordination-Based Tetrahedral Cage

Caged structures have found wide application in a variety of areas, including guest encapsulation and catalysis. Although metal-based cages have dominated the field, anion-coordination-based cages are emerging as a new type of supramolecular ensemble with